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#$Date: 2025-08-21 13:25:49 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301846 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/00/98/7009873.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7009873
loop_
_publ_author_name
'Boyle, Philip D.'
'Christie, Jill'
'Dyer, Thomas'
'Godfrey, Stephen M.'
'Howson, Ian R.'
'McArthur, Christina'
'Omar, Bashie'
'Pritchard, Robin G.'
'Williams, Gareth Rh.'
_publ_section_title
;
 Further structural motifs from the reactions of thioamides with
 diiodine and the interhalogens iodine monobromide and iodine
 monochloride: an FT-Raman and crystallographic study †
;
_journal_issue                   18
_journal_name_full
'Journal of the Chemical Society, Dalton Transactions'
_journal_page_first              3106
_journal_paper_doi               10.1039/b004182n
_journal_year                    2000
_chemical_formula_sum            'C6 H16 I4 N4 S2'
_chemical_formula_weight         715.95
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.29(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.743(3)
_cell_length_b                   16.368(2)
_cell_length_c                   15.231(2)
_cell_measurement_temperature    203(2)
_cell_volume                     3675.4(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6986
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    6.996
_exptl_absorpt_correction_T_max  0.7211
_exptl_absorpt_correction_T_min  0.2737
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.523
_refine_diff_density_min         -2.091
_refine_diff_density_rms         0.242
_refine_ls_extinction_coef       0.00007(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         6451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0831P)²+0.5550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                5126
_reflns_number_total             6451
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b004182n.txt
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7009873
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.67773(6) 0.13654(6) 0.11039(6) 0.0400(2) Uani 1 1 d . . .
I2 I 0.82116(6) 0.86015(5) 0.38470(5) 0.0349(2) Uani 1 1 d . . .
I3 I 0.60587(7) 0.55576(6) 0.40419(6) 0.0446(2) Uani 1 1 d . . .
I4 I 0.57894(6) 0.72991(5) 0.40838(5) 0.0373(2) Uani 1 1 d . . .
I5 I 0.54378(6) 0.90693(6) 0.41165(6) 0.0429(2) Uani 1 1 d . . .
I6 I 0.95277(7) 0.07321(6) 0.14018(6) 0.0490(3) Uani 1 1 d . . .
I7 I 0.92808(6) 0.24819(6) 0.13768(5) 0.0372(2) Uani 1 1 d . . .
I8 I 0.89900(7) 0.42392(6) 0.13629(6) 0.0472(3) Uani 1 1 d . . .
S1 S 0.6365(2) 0.1663(3) -0.0564(2) 0.0438(9) Uani 1 1 d . . .
S2 S 0.7208(3) 0.1081(3) 0.2734(2) 0.0611(12) Uani 1 1 d . . .
S3 S 0.8642(2) 0.8614(3) 0.2178(2) 0.0470(10) Uani 1 1 d . . .
S4 S 0.7777(2) 0.8554(3) 0.5522(2) 0.0495(10) Uani 1 1 d . . .
N1 N 0.8159(7) 0.1452(8) -0.0672(7) 0.050(3) Uani 1 1 d . . .
H1 H 0.8155 0.1503 -0.0104 0.060 Uiso 1 1 calc R . .
N2 N 0.7373(7) 0.1430(7) -0.1956(7) 0.039(3) Uani 1 1 d . . .
H2 H 0.7893 0.1361 -0.2215 0.047 Uiso 1 1 calc R . .
N3 N 0.5420(7) 0.1341(8) 0.2890(7) 0.049(3) Uani 1 1 d . . .
H3 H 0.5416 0.1382 0.2321 0.059 Uiso 1 1 calc R . .
N4 N 0.6236(7) 0.1144(7) 0.4161(7) 0.040(3) Uani 1 1 d . . .
H4 H 0.5724 0.1195 0.4436 0.048 Uiso 1 1 calc R . .
N5 N 0.6844(7) 0.8842(8) 0.2050(7) 0.044(3) Uani 1 1 d . . .
H5 H 0.6850 0.8820 0.2621 0.053 Uiso 1 1 calc R . .
N6 N 0.7640(8) 0.8817(7) 0.0780(6) 0.040(3) Uani 1 1 d . . .
H6 H 0.7127 0.8905 0.0512 0.048 Uiso 1 1 calc R . .
N7 N 0.9589(7) 0.8590(8) 0.5638(7) 0.044(3) Uani 1 1 d . . .
H7 H 0.9587 0.8521 0.5072 0.052 Uiso 1 1 calc R . .
N8 N 0.8821(8) 0.8645(7) 0.6936(6) 0.039(3) Uani 1 1 d . . .
H8 H 0.9339 0.8652 0.7211 0.047 Uiso 1 1 calc R . .
C1 C 0.7380(8) 0.1500(8) -0.1098(9) 0.035(3) Uani 1 1 d . . .
C2 C 0.6559(11) 0.1459(12) -0.2516(10) 0.069(5) Uani 1 1 d . . .
H2A H 0.6143 0.1030 -0.2342 0.104 Uiso 1 1 calc R . .
H2B H 0.6731 0.1381 -0.3124 0.104 Uiso 1 1 calc R . .
H2C H 0.6265 0.1986 -0.2451 0.104 Uiso 1 1 calc R . .
C3 C 0.9026(10) 0.1318(13) -0.1105(10) 0.072(6) Uani 1 1 d . . .
H3A H 0.9046 0.0766 -0.1337 0.108 Uiso 1 1 calc R . .
H3B H 0.9515 0.1392 -0.0685 0.108 Uiso 1 1 calc R . .
H3C H 0.9094 0.1706 -0.1582 0.108 Uiso 1 1 calc R . .
C4 C 0.6210(9) 0.1199(8) 0.3293(8) 0.038(3) Uani 1 1 d . . .
C5 C 0.4561(10) 0.1430(11) 0.3355(10) 0.058(5) Uani 1 1 d . . .
H5A H 0.4394 0.0911 0.3616 0.088 Uiso 1 1 calc R . .
H5B H 0.4093 0.1601 0.2946 0.088 Uiso 1 1 calc R . .
H5C H 0.4628 0.1838 0.3813 0.088 Uiso 1 1 calc R . .
C6 C 0.7031(10) 0.1007(11) 0.4691(10) 0.058(4) Uani 1 1 d . . .
H6A H 0.7327 0.0508 0.4505 0.086 Uiso 1 1 calc R . .
H6B H 0.6857 0.0959 0.5302 0.086 Uiso 1 1 calc R . .
H6C H 0.7445 0.1463 0.4624 0.086 Uiso 1 1 calc R . .
C7 C 0.7612(8) 0.8779(8) 0.1636(8) 0.033(3) Uani 1 1 d . . .
C8 C 0.5998(9) 0.8946(12) 0.1615(9) 0.060(5) Uani 1 1 d . . .
H8A H 0.6006 0.9451 0.1282 0.090 Uiso 1 1 calc R . .
H8B H 0.5516 0.8968 0.2046 0.090 Uiso 1 1 calc R . .
H8C H 0.5894 0.8490 0.1220 0.090 Uiso 1 1 calc R . .
C9 C 0.8422(9) 0.8729(10) 0.0235(10) 0.050(4) Uani 1 1 d . . .
H9A H 0.8865 0.9144 0.0388 0.076 Uiso 1 1 calc R . .
H9B H 0.8246 0.8792 -0.0376 0.076 Uiso 1 1 calc R . .
H9C H 0.8684 0.8192 0.0322 0.076 Uiso 1 1 calc R . .
C10 C 0.8823(9) 0.8607(9) 0.6050(8) 0.038(3) Uani 1 1 d . . .
C11 C 1.0449(9) 0.8681(11) 0.6088(9) 0.057(4) Uani 1 1 d . . .
H11A H 1.0431 0.9163 0.6458 0.086 Uiso 1 1 calc R . .
H11B H 1.0929 0.8740 0.5660 0.086 Uiso 1 1 calc R . .
H11C H 1.0563 0.8203 0.6448 0.086 Uiso 1 1 calc R . .
C12 C 0.7977(10) 0.8677(12) 0.7466(9) 0.061(5) Uani 1 1 d . . .
H12A H 0.7684 0.9202 0.7383 0.092 Uiso 1 1 calc R . .
H12B H 0.8127 0.8605 0.8082 0.092 Uiso 1 1 calc R . .
H12C H 0.7570 0.8245 0.7279 0.092 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S2 I1 S1 179.07(12) . . ?
S3 I2 S4 178.75(14) . . ?
I3 I4 I5 177.77(4) . . ?
I6 I7 I8 178.72(4) . . ?
C1 S1 I1 103.2(4) . . ?
C4 S2 I1 104.3(5) . . ?
C7 S3 I2 104.2(4) . . ?
C10 S4 I2 103.1(4) . . ?
C1 N1 C3 123.3(12) . . ?
C1 N2 C2 125.3(12) . . ?
C4 N3 C5 123.5(11) . . ?
C4 N4 C6 126.2(12) . . ?
C7 N5 C8 123.1(11) . . ?
C7 N6 C9 127.2(12) . . ?
C10 N7 C11 122.2(11) . . ?
C10 N8 C12 123.4(11) . . ?
N2 C1 N1 119.2(12) . . ?
N2 C1 S1 118.7(9) . . ?
N1 C1 S1 122.1(10) . . ?
N4 C4 N3 119.4(12) . . ?
N4 C4 S2 117.8(10) . . ?
N3 C4 S2 122.7(10) . . ?
N5 C7 N6 120.8(11) . . ?
N5 C7 S3 122.6(9) . . ?
N6 C7 S3 116.6(10) . . ?
N7 C10 N8 119.4(12) . . ?
N7 C10 S4 123.3(9) . . ?
N8 C10 S4 117.3(10) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 S2 2.602(4) . ?
I1 S1 2.654(4) . ?
I2 S3 2.623(4) . ?
I2 S4 2.634(4) . ?
I3 I4 2.8787(13) . ?
I4 I5 2.9440(13) . ?
I6 I7 2.8874(14) . ?
I7 I8 2.9082(14) . ?
S1 C1 1.728(13) . ?
S2 C4 1.715(14) . ?
S3 C7 1.747(12) . ?
S4 C10 1.737(13) . ?
N1 C1 1.318(16) . ?
N1 C3 1.458(17) . ?
N2 C1 1.312(16) . ?
N2 C2 1.470(17) . ?
N3 C4 1.334(16) . ?
N3 C5 1.461(17) . ?
N4 C4 1.326(16) . ?
N4 C6 1.436(16) . ?
N5 C7 1.303(15) . ?
N5 C8 1.419(16) . ?
N6 C7 1.305(16) . ?
N6 C9 1.431(16) . ?
N7 C10 1.295(17) . ?
N7 C11 1.445(16) . ?
N8 C10 1.352(15) . ?
N8 C12 1.487(16) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139153892
